Wagner-Meerwein rearrangements in the gas phase: Deuterium isotope effects on acid-induced dissociation of optically active phenylpropanols

Chemistry - A European Journal

Volumn 5, Issue 3, 1999, Pages 845-853

  Speranza, Maurizio ^a   Filippi, Antonello ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Anchimeric assistance; Chirality; Gas phase chemistry; Kinetic isotope effects; Phenonium ions

Indexed keywords

PHENYL GROUP; PROPANOL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIMERA; CHIRALITY; CONFORMATION; GAS ANALYSIS; KINETICS; OPTICAL ROTATION; REACTION ANALYSIS;

EID: 0033038204     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19990301)5:3<845::aid-chem845>3.0.co;2-8     Document Type: Article

References (45)

1. A. Filippi, M. Speranza, Chem. Eur. J. 1999, 5, 834-844.
2. a) D. J. Cram, J. Am. Chem. Soc. 1949, 71, 3863;
3. b) D. J. Cram, R. Davis, J. Am. Chem. Soc. 1949, 71, 3875;
4. c) D. J. Cram, J. Am. Chem. Soc. 1964, 86, 3767;
5. d) C. J. Lancelot, D. J. Cram, P. von R. Schleyer, Carbonium Ions, Vol. III (Eds.: G. A. Olah, P. von R. Schleyer) Wiley, New York, 1972, chapter 27;
6. e) S. Winstein, B. K. Morse, E. Grunwald, K. C. Schreiber, J. Corse, J. Am. Chem. Soc. 1952, 74, 1113.
7. a) H. C. Brown, The Transition State, Special Publ. No. 16, The Chemical Society, London, 1962, p. 149;
8. b) H. C. Brown, K. J. Morgan, F. J. Cloupek, J. Am. Chem. Soc. 1965, 87, 2137.
9. a) H. C. Brown, R. Bernheimer, C. J. Kim, S. E. Scheppele, J. Am. Chem. Soc. 1967, 89, 370;
10. b) H. C. Brown, C. J. Kim, J. Am. Chem. Soc. 1968, 90, 2080;
11. c) W. H. Saunders Jr., S. Asperger, D. H. Edison, J. Am. Chem. Soc. 1958, 80, 2421;
12. d) S. L. Loukas, M. R. Velkou, G. A. Gregoriou, J. Chem. Soc. Chem. Commun. 1969, 1199;
13. e) S. L. Loukas, F. S. Varveri, M. R. Velkou, G. A. Gregoriou, Tetrahedron Lett. 1971, 1803.
14. B. Capon, S. P. McManus, Neighboring Group Participation Vol. 1, Plenum, New York, 1976.
15. a) D. E. Sunko, S. Borcic, Isotope Effects in Chemical Reactions (Eds.: C. J. Collins, N. S. Bowman), Van Nostrand Reinhold, New York, 1970, chapter 3;
16. b) V. J. Shiner, Jr., Isotope Effects in Chemical Reactions (Eds.: C. J. Collins, N. S. Bowman), Van Nostrand Reinhold, New York, 1970, chapter 2;
17. c) S. E. Scheppele, Chem. Rev. 1972, 72, 511.
18. a) W. H. Saunders, Jr., R. Glaser, J. Am. Chem. Soc. 1960, 82, 3586;
19. b) D. J. Cram, J. Tadanier, J. Am. Chem. Soc. 1959, 81, 2737;
20. c) C. C. Lee, L. Noszko, Can. J. Chem. 1966, 44, 2491.
21. a) K. Funatsu, M. Fujio, Y. Tsuno, Mem. Fac. Sci. Kyushu Univ. Ser. C 1981, 13, 125;
22. b) K. Funatsu, M. Kimura, T. Furukama, M. Fujio, Y. Tsuno, Mem. Fac. Sci. Kyushu Univ. Ser. C 1984, 14, 343.
23. H. C. Brown, G. Zweifel, J. Am. Chem. Soc. 1960, 82, 4708.
24. D. Achet, D. Rocrelle, I. Murengezi, M. Delmas, A. Gaset, Synthesis 1986, 643.
25. a) P. Ausloos, S. G. Lias, R. Gorden, Jr., J. Chem. Phys. 1963, 39, 3341;
26. b) P. Ausloos, Ion-Molecule Reactions (Ed.: J. L. Franklin), Plenum, New York, 1970;
27. c) P. Ausloos, S. G. Lias, J. Chem. Phys. 1962, 36, 3163;
28. d) S. G. Lias, P. Ausloos, J. Chem. Phys. 1962, 37, 877.
29. +] to methanol, may proceed through several pathways, including proton transfer to the substrate itself, to the walls of the reaction vessel, or to adventitious bases that are either initially added to the gaseous mixture or formed by its radiolysis.
30. 15=1.04, where no differences in factors i) and ii) are present and, therefore, the only rate difference is due to factor iii).
31. a) S. S. Glad, F. Jensen, J. Am. Chem. Soc. 1994, 116, 9302, and references therein;
32. b) X. Duan, S. Scheiner, J. Am. Chem. Soc. 1992, 114, 5849.
33. a) S. S. Glad, F. Jensen, J. Am. Chem. Soc. 1997, 119, 227, and references therein;
34. b) K. C. Westaway, T. V. Pham, Y. Fang, J. Am. Chem. Soc. 1997, 119, 3670, and references therein.
35. a) S. E. Scheppele, Chem. Rev. 1972, 72, 511, and references therein;
36. b) D. J. DeFrees, M. Taagepera, B. A. Levi, S. K. Pollack, K. D. Summerhays, R. W. Taft, M. Wolfsberg, W. J. Hehre, J. Am. Chem. Soc. 1979, 101, 5532.
37. 1-SKIE on the ethanolysis of cis-4-tert-butylcyclohexyl brosylate amounts to 1.436, when the β-D is axial, and to 1.096, when the β-D is equatorial (V. J. Shiner, Jr., J. G. Jewett, Jr., J. Am. Chem. Soc. 1965, 87, 1382).
38. 1-SKIE on the ethanolysis of cis-4-tert-butylcyclohexyl brosylate amounts to 1.436, when the β-D is axial, and to 1.096, when the β-D is equatorial (V. J. Shiner, Jr., J. G. Jewett, Jr., J. Am. Chem. Soc. 1965, 87, 1382).
39. J. L. Fry, G. J. Karabatsos, Carbonium Ions (Eds.: G. A. Olah, P. von R. Schleyer) Wiley, New York, 1970, p. 526. See also: a) F. Cacace, M. E. Crestoni, S. Fornarini, J. Am. Chem. Soc. 1992, 114, 6776;
40. J. L. Fry, G. J. Karabatsos, Carbonium Ions (Eds.: G. A. Olah, P. von R. Schleyer) Wiley, New York, 1970, p. 526. See also: a) F. Cacace, M. E. Crestoni, S. Fornarini, J. Am. Chem. Soc. 1992, 114, 6776;
41. b) M. E. Crestoni, S. Fornarini, M. Lentini, M. Speranza, J. Phys. Chem. 1996, 100, 8285.
42. M. F. Hawthorne, E S. Lewis, J. Am. Chem. Soc. 1958, 80, 4296.
43. D. Liotta, M. Saindane, L. Waykole, J. Stephens, J. Grossman, J. Am. Chem. Soc. 1988, 110, 2667.
44. + bond elongation.
45. Ph, may not only reflect later TS structures, but also a less extensive frontside participation.